2-[3-(2-Hydroxyphenyl)acryloyl]benzoic acid → HCID 12260520, compound

HRID 1678967Notes

Reaction equation

HRID 1678967 reaction equation
O[C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH:4]=[CH:5][C:6]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])=[O:7]>O>[C:10]1([C:9]2[C:8](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]2([CH:5]=[CH:4][C:3]3[C:17](=[CH:18][CH:19]=[CH:20][CH:2]=3)[O:7]2)[O:12]1)=[O:11]

Participants

3

Reactant 1

HCID 544201342-[3-(2-Hydroxyphenyl)acryloyl]benzoic acid

Product 1

HCID 12260520HCID 12260520, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.7 g of o-(o-hydroxycinnamoyl)benzoic acid was heated in 100 ml of N-dimethylformamide under agitation for 6 hours. Then, the liquid reaction mixture was poured into 400 ml of water to form a white crystal. The crystal was recovered by filtration and recrystallized from ethyl alcohol to obtain 10.7 g of 2H-chromene-2-spiro-3'-phthalide (compound (1)) as a colorless needle. (yield = 90%). Physical properties of the product are as follows:

Workup

  1. customThen, the liquid reaction mixture
  2. customto form a white crystal
  3. filtrationThe crystal was recovered by filtration
  4. customrecrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-a7432eac3bf84dc991dfd0ca0138942a
Source dataset
uspto-grants-1978_03
Patent number
US04078074

Reaction notes

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